Herbicide composition

ABSTRACT

The present invention relates to a herbicidal composition containing as active ingredients 2-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]propionic acid ester, and glyphosate or its salt, and a method for controlling weeds comprising applying it to weeds. The herbicidal effect in the case where the present composition applied is synergistically increased compared with the cases where the each active ingredient is independently applied, therefore the present composition can control effectively a variety of weeds.

This application is the national phase under 35 U.S.C. §371 of PCTInternational Application No. PCT/JP00/03460 which has an Internationalfiling date of May 29, 2000, which designated the United States ofAmerica.

TECHNICAL FIELD

The present invention relates to a herbicidal composition, especially, aherbicidal composition suitable for controlling weeds in fields of corn.

BACKGROUND ART

At the present time, numerous herbicides are commercially available andused. There are, however, many species of weeds to be controlled andtheir growth extends over a long time. For this reason, requested areherbicides with higher herbicidal activity, wider herbicidal spectrum,and no problems for phytotoxicity to crops.

DISCLOSURE OF INVENTION

The present inventor has intensively studied to find out excellentherbicides. As a result, he has found that various weeds growing in croplands or non-crop lands can be effectively controlled by a herbicidalcomposition containing as active ingredients,2-[2-chloro-4-fluoro-5-{3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl}phenoxy]propionicacid ester (hereinafter, referred to as the present ester) andN-(phosphonomethyl)glycine (common name; glyphosate, hereinafter,referred to as glyphosate) or its salt. He has further found that theherbicidal activity is synergistically increased as compared with thecases where the active ingredient are independently used, and theherbicidal composition can, therefore, be applied at a lower amount; andthat the herbicidal spectrum is expanded and especially, a wide varietyof weeds in fields of corn can be controlled, thereby completing thepresent invention.

Thus, the present invention provides a herbicidal composition comprisingas active ingredients, the present ester and glyphosate or its salt(hereinafter referred to as the present composition); and a method forcontrolling weeds which comprises applying them to weeds.

THE BEST MODE FOR CARRYING OUT THE INVENTION

The present ester which is one active ingredient of the presentcomposition represents C1-C7 alkylester, C5-C6 cycloalkylester, C3-C6alkenylester and the like. These compounds can be produced according tothe method described in the following production example.

PRODUCTION EXAMPLE 1

In 70 ml of N,N-dimethylformamide, 6.7 g of3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedionewas dissolved, and 4.2 g of potassium carbonate and 3.3 ml of methyl2-chloropropionate were added to the solution, and then that was stirredfor 1 hour at room temperature and for 45 minutes at 100° C. Thereafter,the reaction solution was poured into water, and that was extracted withethyl acetate. The organic layer was washed with saturated sodiumchloride solution, and after drying over anhydrous magnesium sulfate,was concentrated. The residue was subjected to silica gel columnchromatography (eluent, hexane/ethyl acetate=3/1), and 5.82 g of methyl2-[2-chloro-4-fluoro-5-{3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl}phenoxy]propionate(hereinafter referred to as the compound A) was obtained.

The present ester except for the compound A can be obtained byconducting the similar operations as described in the above productionexample 1, with the exception of using the reaction reagent, examplesdescribed in the following table 1, in replace of methyl2-chloropropionate.

Some of the present ester obtained by such methods are shown with thatreaction reagent.

TABLE 1

Compound symbol R Reaction Reagent B propyl Propyl 2-bromopropionate Cbutyl Butyl 2-bromopropionate D pentyl Pentyl 2-bromopropionate E hexylHexyl 2-bromopropionate F heptyl Heptyl 2-bromopropionate G i-propyli-Propyl 2-bromopropionate H i-butyl i-Butyl 2-bromopropionate I t-butylt-Butyl 2-bromopropionate J c-pentyl c-Pentyl 2-bromopropionate Kc-hexyl c-Hexyl 2-bromopropionate L allyl Allyl 2-bromopropionate Methyl Ethyl 2-bromopropionate (In this table, “i-” represents iso, “t-”represents tertiary, and “c-” represents cyclo.)

Compound A

¹H-NMR(CDCl₃,300 Mz): δ (ppm)7.31(1H,d,J=9.0 Hz),6.82(1/2H, d,J=6.42Hz),6.81(1/2H,d,J=6.45 Hz),6.35(1H,s),4.68(1H,q,J=6.9Hz),3.74(3H,s),3.55(3H,s,br),1.66(3H,d,J=6.9 Hz)

Compound H

¹H-NMR(CDCl₃,250 Mz): δ (ppm)7.31(1H,d,J=8.9 Hz),6.82(1/2H, d,J=6.5Hz),6.81(1/2H,d,J=6.4Hz),6.34(1H,s),4.70(1H,brq,J=6.8Hz),3.98-3.85(2H,m),3.54(3H,q,J=1.2Hz)1.90(1H,m),1.68(3H,d,J=6.8 Hz)0.862(3H,d,J=6.7 Hz),0.858(3H,d,J=6.7Hz)

Compound K

¹H-NMR(CDCl₃,300 Mz): 7.30(1H,d,J=8.9 Hz),6.82(1/2H,d,J=6.5Hz),6.81(1/2H,d,J=6.4 Hz),6.33(1H,d,J=1.5 Hz),4.82(1H,m),4.66(1H,q,J=6.7Hz),3.55-3.53(3H,m),1.90-1.30(10H,m),1.66(3H,d,J=6.81 Hz)

Compound L

¹H-NMR(CDCl₃,300 Mz): δ (ppm)7.31(1H,d,J=8.9 Hz),6.84(1/2H, d,J=6.50Hz),6.82(1/2H,d,J=6.41 Hz),6.34(1H,s),5.91-5.80(1H,m), 5.29(1H,ddd,J=1.1Hz,1.1 Hz,17.1 Hz),5.22(1H,dd,J=1.1 Hz,10.7 Hz), 4.71(1H,q,J=7.1Hz),4.64(2H,dd,J=1.1 Hz,5.6 Hz),3.55(3H,t,J=1.45 Hz),1.68(3H,d,J=7.1 Hz)

Glyphosate and its salts are compounds described in Farm ChemicalsHandbook, 1995 (Meister Publishing Co., 1995) page C188. The salts forthe present invention mean all the agriculturally acceptable salts, andisopropylamine salt, trimesium salt, ammonium salt and the like can beexemplified.

The present composition has a herbicidal effect to a variety of weeds.Examples of the weeds are shown below.

Polygonaceous weeds:

wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonumlapathifolium), pennsylvania smartweed (Polygonum pensylvanicum),ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleafdock (Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatum)

Portulacaceous weeds:

common purslane (Portulaca oleracea)

Caryophyllaceous weeds:

common chickweed (Stellaria media)

Chenopodiaceous weeds:

common lambsquarters (Chenopodium album), kochia (Kochia scoparia)

Amaranthaceous weeds:

redroot pigweed (Amaranthus retroflexus), smooth pigweed (Amaranthushybridus)

Cruciferous (brassicaceous) weeds:

wild radish (Raphanus raphanistrum), wild mustard (Sinapis arvensis),shepherdpurse (Capsella bursa-pastoris)

Leguminous (fabaceous) weeds:

hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia) ,Florida beggarweed (Desmodium tortuosum), white clover (Trifoliumrepens)

Malvaceous weeds:

velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa)

Violaceous weeds:

field pansy (Viola arvensis), wild pansy (Viola tricolor)

Rubiaceous weeds: catchweed bedstraw (cleavers) (Galium aparine)

Convolvulaceous weeds:

ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoeapurpurea), entireleaf morningglory (Ipomoea hederacea var.integriuscula), pitted morningglory (Ipomoea lacunosa), field bindweed(Convolvulus arvensis)

Labiate weeds:

red deadnettle (Lamium purpureum), henbit (Lamium amplexicaule)

Solanaceous weeds:

jimsonweed (Datura stramonium), black nightshade (Solanum nigrum)

Scrophulariaceous weeds:

birdseye speedwell (Veronica persica), ivyleaf speedwell (Veronicahederaefolia)

Composite weeds:

common cocklebur (Xanthium pensylvanicum), common sunflower (Helianthusannuus), scentless chamomile (Matricaria perforata or inodora), cornmarigold (Chrysanthemum segetum), pineappleweed (Matricariamatricarioides), common ragweed (Ambrosia artemisiifolia), giant ragweed(Ambrosia trifida), horseweed (Erigeron canadensis), Japanese mugwort(Artemisia princeps), tall goldenrod (Solidago altissima)

Boraginaceous weeds:

forget-me-not (Myosotis arvensis)

Asclepiadaceous weeds:

common milkweed (Asclepias syriaca)

Euphorbiaceous weeds:

sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbia maculata)

Graminaceous weeds:

barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis),giant foxtail (Setaria faberi), large crabgrass (Digitaria sanguinalis),goosegrass (Eleusine indica), annual bluegrass (Poa annua), blackgrass(Alopecurus myosuroides), wild oat (Avena fatua), johnsongrass (Sorghumhalepense), quackgrass (Agropyron repens), downy brome (Bromustectorum), bermudagrass (Cynodon dactylon), fall panicum (Panicumdichotomiflorum), Texas panicum (Panicum texanum), shattercane (Sorghumvulgare)

Commelinaceous weeds:

common dayflower (Commelina communis)

Equisetaceous weeds:

field horsetail (Equisetum arvense)

Cyperaceous weeds:

rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus),yellow nutsedge (Cyperus esculentus)

The present composition may be used as a herbicide, because of havingherbicidal activities for a wide variety of weeds. The presentcomposition gives excellent herbicidal effect, in which case the presentcomposition are used in agricultural field, such as corn field, soybeanfield and the like, and non-agricultural field, such as orchard,horticultural field, play ground, vacant lot, wood, railroad side andthe like.

The present composition can be used for till cultivation and no-tillcultivation in the agricultural field. Especially the presentcomposition can attain effective control of the wide variety of weedsgrowing between winter and spring and do not cause a problematicphytotoxicity against corn seeded after applying the present compositionin which case the present composition was applied in the no-tillagecultivated corn field before seeding.

In the present composition, the mixing ratio of the present ester andglyphosate or its salt as active ingredients, although it may vary withthe species of weeds to be controlled, situation and conditions ofapplication and the like, is usually 1:1 to 500, preferably 1:2 to 100by weight.

The present composition may be usually used in the form of formulationssuch as emulsifiable concentrates, wettable powders, flowables, granulesand the like which can be prepared by mixing with solid carriers, liquidcarriers, and the like, and if necessary, adding surfactants, otheradjuvants and the like. In such a formulation, the present ester andglyphosate or its salt are usually contained at the total amount of 0.5to 90% by weight, preferably 1 to 80% by weight.

The solid carrier to be used in the formulation may include, forexample, the following materials in fine powder or granule form: clays(e.g., kaolinite, diatomaceous earth, synthetic hydrated silicon oxide,Fubasami clay, bentonite, acid clay); talc and other inorganic minerals(e.g., sericite, powdered quartz, powdered sulfur, activated carbon,calcium carbonate); and chemical fertilizers (e.g., ammonium sulfate,ammonium phosphate, ammonium nitrate, ammonium chloride, urea). Theliquid carrier may include, for example, water; alcohols (e.g.,methanol, ethanol); ketones (e.g., acetone, methyl ethyl ketone,cyclohexanone); aromatic hydrocarbons (e.g., toluene, xylene,ethylbenzene, methylnaphthalene); non-aromatic hydrocarbons (e.g.,hexane, cyclohexane, kerosine); esters (e.g., ethyl acetate,butylacetate); nitriles (e.g., acetonitrile, isobutyronitrile); ethers(e.g., dioxane, diisopropyl ether); acid amides (e.g.,dimethylformamide, dimethylacetamide); and halogenated hydrocarbons(e.g., dichloroethane, trichloroethylene).

The surfactant may include, for example, alkylsulfric acid esters;alkylsulfonic acid salts; alkylarylsulfonic acid salts; alkyl arylethers and their polyoxyethylene derivatives; polyethylene glycolethers; polyhydric alcohol esters; and sugar alcohol derivatives.

The other adjuvants may include, for example, adhesive agents anddispersing agents, such as casein, gelatin, polysaccharides (e.g.,starch, gum arabic, cellulose derivatives, alginic acid), ligninderivatives, bentonite, and synthetic water-soluble polymers (e.g.,polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid); andstabilizers such as PAP (isopropyl acid phosphate), BHT(2,6-di-tert-butyl-4-methylphenol), BHA(2-/3-tert-butyl-4-methyoxyphenol), vegetable oils, mineral oils, fattyacids, and fatty acid esters.

The present composition can also be prepared by making each activeingredient into the above formulation and then mixing theseformulations.

The present composition thus formulated may be applied to the plant assuch, or after diluted with water or the like. Further, the presentcomposition may also be used in admixture with other herbicides, inwhich case the herbicidal effect can be expected to be enhanced.Furthermore the present composition can also be used together withinsecticides, fungicides, plant growth regulators, fertilizers orsafener.

The application amount of the present composition, although it may varywith the mixing ratio of the present ester and glyphosate or its salt asthe active ingredient compounds, weather conditions, formulation types,application times, application methods, application places, weeds to becontrolled, and crops to be protected, is usually 10 to 8000 g,preferably 100 to 4000 g as the total amount of active ingredientcompounds per hectare. In the case of emulsifiable concentrates,wettable powders, flowables, or the like, they are usually applied afterdiluted in their prescribed amounts with water at a ratio of 100 to 1000liters per hectare. Also, in case of foliar treatment of the presentcomposition to weeds, the dilution of the present composition with waterin which the adjuvant is added may be expected to enhance the effectagainst weeds.

The following will describe formulation examples, in which parts are byweight.

Formulation Example 1

Four (4) parts of compound A, B, C, D, E, F, G, H, I, J, K, L or M, 80parts of glyphosate or its salt, 3 parts of calcium lignin sulfonate, 2parts of sodium laurylsulfate, and 11 parts of synthetic hydratedsilicon oxide are well pulverized and mixed to give a wettable powder.

Formulation Example 2

Twenty (20) parts of compound A, B, C, D, E, F, G, H, I, J, K, L or M,20 parts of glyphosate or its salt, 3 parts of calcium lignin sulfonate,2 parts of sodium laurylsulfate, and 55 parts of synthetic hydratedsilicon oxide are well pulverized and mixed to give a wettable powder.

Formulation Example 3

One-tenth (0.1) part of compound A, B, C, D, E, F, G, H, I, J, K, L orM, 50 parts of glyphosate or its salt, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate, and 44.9 parts of synthetichydrated silicon oxide are well pulverized and mixed to give a wettablepowder.

Formulation Example 4

Two (2) parts of compound A, B, C, D, E, F, G, H, I, J, K, L or M, 20parts of glyphosate or its salt, 3 parts of calcium lignin sulfonate, 2parts of sodium laurylsulfate, and 73 parts of synthetic hydratedsilicon oxide are well pulverized and mixed to give a wettable powder.

Formulation Example 5

Two (2) parts of compound A, B, C, D, E, F, G, H, I, J, K, L or M, 40parts of glyphosate or its salt, 3parts of polyoxyethylene sorbitanmonooleate, 3 parts of CMC (carboxymethylcellulose), and 52 parts ofwater are mixed and wet pulverized until the particle size comes to 5microns or smaller to give a flowable.

Formulation Example 6

Ten (10) parts of compound A, B, C, D, E, F, G, H, I, J, K, L or M, 10parts of glyphosate or its salt, 3 parts of polyoxyethylene sorbitanmonooleate, 3 parts of CMC (carboxymethylcellulose), and 74 parts ofwater are mixed and wet pulverized until the particle size comes to 5microns or smaller to give a flowable.

Formulation Example 7

Zero point zero one (0.05) part of compound A, B, C, D, E, F, G, H, I,J, K, L or M, 25 parts of glyphosate or its salt, 3 parts ofpolyoxyethylene sorbitan monooleate, 3 parts of CMC(carboxymethylcellulose), and 68.95 parts of water are mixed and wetpulverized until the particle size comes to 5 microns or smaller to givea flowable.

Formulation Example 8

One (1) part of compound A, B, C, D, E, F, G, H, I, J, K, L or M, 10parts of glyphosate or its salt, 3 parts of polyoxyethylene sorbitanmonooleate, 3 parts of CMC (carboxymethylcellulose), and 83 parts ofwater are mixed and wet pulverized until the particle size comes to 5microns or smaller to give a flowable.

The following will describe test examples.

Evaluation Criteria

The herbicidal effect is evaluated at 11 levels with indices of 0 to 10,i.e., shown by numeral “0”, “1”, “2”, “3”, “4”, “5”, “6”, “7”, “8”, “9”,or “10”, wherein “0” means that there was no or little difference in thedegree of germination or growth between the treated plants and theuntreated plants at the time of examination, and “10” means that thetest plants died completely or their germination or growth wascompletely inhibited. The values, “7”, “8”, “9”, and “10” of theherbicidal effect mean a excellent herbicidal effect.

The phytotoxicity is evaluated like these, “no harm” means that thephytotoxicity was unrecognizable or almost unrecognized, “small” meansthat a slight degree of phytotoxicity was recognized, “medium” meansthat a medium degree of phytotoxicity was recognized, and “large” meansthat a large degree of phytotoxicity was recognized.

Test Example 1

Plastic pots each having a diameter of 11 cm and a depth of 8 cm werefilled with upland soil, and then buried tubers of yellow nutsedge. Andtest plants were given 26 days to grow in greenhouse.An emulsifiableconcentrate of compound A which had been obtained by well mixing 5 partsof compound A, 6 parts of Sorpol 3005X (produced by Toho ChemicalIndustry, Co., Ltd.) and 89 parts of xylene, a formulated glyphosateproduct (trade name: Roundup; seller, Monsanto Japan Limited), and amixture of the emulsifiable concentrate of compound A and the formulatedglyphosate product were independently diluted in their prescribedamounts with water. Each dilution was uniformly sprayed over the plantswith a small sprayer, and then corn was further seeded. After theapplication the test plants were grown in the greenhouse for further 10days and then, herbicidal activity and phytotoxicity to corn wereexamined. The results are shown in Table 2.

TABLE 2 Herbicidal activity Dosage Yellow Phytotoxicity Test Compound(g/ha) nutsedge Corn Compound A 120 4 no harm Glyphosate 560 1 no harmisopropylamine salt Compound A + 120 + 9 no harm Glyphosate 560isopropylamine salt

Industrial Applicability

The present composition have excellent herbicidal effect against avariety of weeds, especially it can control a wide variety of weeds infields of corn selectively.

What is claimed is:
 1. A herbicidal composition containing as activeingredients,2-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]propionicacid ester, and N-(phosphonomethyl)glycine or its salt.
 2. Theherbicidal composition according to claim 1, wherein the ester is C1-C7alkylester, C5-C6 cycloalkylester or C3-C6 alkenylester.
 3. Theherbicidal composition according to claim 1, wherein the ester is C1-C7alkylester.
 4. The herbicidal composition according to claim 1, whereinthe ester is methyl ester.
 5. The herbicidal composition according toany one of claims 1 to 4, wherein the weight ratio of the ester toN-(phosphonomethyl)glycine or its salt is from 1:1 to 1:500.
 6. Thecomposition of claim 1, further comprising at least one member from thegroup consisting of solid carriers, liquid carriers, surfactants andadjuvants.
 7. A method for controlling weeds, which comprises applyingthe composition according to claim 1 to weeds.
 8. The method forcontrolling weeds according to claim 7, wherein the weeds are thosegrown in fields of corn.
 9. The method for controlling weeds accordingto claim 7, wherein the total amount of the active ingredient compoundsper hectare is 10 to 8000 g.
 10. The method according to claim 9,wherein the total amount of the active ingredient compounds per hectareis 100 to 4000 g.
 11. The method according to claim 7, wherein saidweeds are those grown in fields of soybean or corn.
 12. The methodaccording to claim 7, wherein said weeds are those grown innon-agricultural areas.